


Five times Cas tried to prank Dean and it didn't turn out the way he expected.

by elisa_anya



Category: Supernatural
Genre: 5 Things, 5 Times, Alternate Universe - Roommates/Housemates, Castiel and Dean Winchester are Roommates, First Kiss, Five Times, Fluff, Fluff and Humor, Friends to Lovers, Humor, Lingerie, M/M, Masturbation, Pranks and Practical Jokes, Roommates, five things
Language: English
Status: Completed
Published: 2018-10-04
Updated: 2018-10-04
Packaged: 2019-07-25 05:49:17
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16191350
Author URL: https://archiveofourown.org/users/elisa_anya/pseuds/elisa_anya
Summary: Each time Cas tries to prank Dean, it comes back to either bite him in the ass or surprise him.





	Five times Cas tried to prank Dean and it didn't turn out the way he expected.

1

The first time Castiel tries to prank Dean, they accidentally end up becoming roommates.

Dean’s away for the weekend visiting his family back in Lawrence, so Castiel, his best friend who has an extra key to his apartment, decides it’s the perfect time to prank him. Dean and Charlie have played endless pranks on him and he’s tired of taking it without ever striking back. They need to know he means business, that they can’t just keep messing with him forever without any consequences. They’re right, he’s not the type of person who pranks other people, he doesn’t have the heart to do anything that might seriously upset or inconvenience someone, he’s too mindful of other people’s feelings, and he’s not very creative when it comes to ways of screwing with his friends because he’s a goodie goodie at heart, but he’s going to prove Dean he’s not just a sweet little angel.

Gabe, his brother and roommate, is moving out of their apartment and into Kali’s, his girlfriend. He tells Castiel to keep his furniture for whoever takes his place at the apartment after he’s gone, that he doesn’t mind, but Castiel puts it all to better use, taking the opportunity to do something else. With Gabriel’s help, he rents a van and takes his brother’s ex single bed, dresser, desk and chair to Dean’s. He goes to his friend’s second bedroom, which he uses as a storage room and also a place where he “works out” (Castiel uses air quotes because he has _never_ seen Dean working out there, not once, even though he spends a serious amount of time there) and empties it. He’s considerate enough to actually properly organise all of Dean’s crap throughout the apartment, so it’s just not laying around on the floor during the prank, then he puts all the new furniture inside the bedroom. Then he proceeds to move all his smaller belongings, like his clothes, books, photographs, posters, the bed sheets, his many types of teas… He puts everything there until it looks like he’s living there and he smiles, utterly satisfied with himself.

“Dean’s going to flip out,” he declares himself victorious ahead of time.

“Is he though?” Gabriel mumbles behind him, not loud enough that his brother hears him.

Castiel knows exactly when Dean’s coming home and he waits for him in ‘his bedroom’, on purpose, lying on the bed with a smug smirk, or the closest thing to it Cas can produce while Gabe sits on the chair (he wasn’t about to lose Dean’s reaction after helping his brother move all that furniture around). When he hears Dean come in, he calls him into the room. Seconds later Dean’s opening the door and his eyes widen in surprise as he looks around the room.

“What the- Cas, what is all of this doing here?” he asks.

Cas lifts an eyebrow, all smug, just waiting for Dean to go nuts so he can take pride and satisfaction from his annoyance. That’ll show him not to mess with a Novak anymore. “You told me I practically lived here since I’m over all the time, so…”

Cas waits and waits, expecting him to get angry or to just laugh, but either way to tell him to move everything right about now and put his stuff back where they go…

But then Dean just shrugs, looking around the room while he nods to himself with the corners of his lips turned downwards, seemingly quite pleased with the situation, and he says, “yeah, you're right. You’ve done a nice job with the room too. You shouldn’t have bothered organising all my shit, though, I gotta throw most of that anyway, bro.”

Castiel’s face falls.

“Wait, you're not angry?”

“My landlord warned me he’s about to raise my rent, I could use a roommate to split the cost and you're always eating my food anyway, so why not? And with Gabe moving out of your apartment, it just makes sense to join forces, doesn’t it?” Dean explains. And Castiel is stunned because, _dammit_ , it _does_ make sense, why hadn’t he thought about that before? He’d been delaying putting up an ad online because he hated the idea of interviewing strangers for the extra room he now had in his apartment, so this solution, moving in with his best friend, was more than ideal and great for his social anxiety. “Great idea, Cas. I would have asked you first, I just didn't know you were willing to move out of your apartment.”

Dean turns on his heels and leaves with an honestly satisfied, happy smile on his face.

Castiel just sits there in his bed with a confused expression on his face. His seriously official bed, in his new apartment he shared with Dean.

“But… but this was supposed to be a prank,” he mutters to the empty space where Dean had been seconds ago.

Gabe laughs and pats his shoulder. “Looks like you live here now.”

2

The second time he pranks Dean, he makes sure to do it with something his friend will find unpleasant but it only ends up making _Castiel_ anxious and feeling terrible.

A friend of his who Dean doesn’t know has asked him to take care of his dog for a week while he’s away on vacations. Normally, he’d say no because Dean has a firm policy against pets, but the whole idea is to piss him off and the pup is a small (though quite fat), pretty well behaved thing, so he accepts and brings the animal over to their apartment.

Dean’s out working when Cas brings Ozzy home. He’s got his water and food bowls, his little bed and his leash. He’s going to let the dog sleep on the couch just to piss Dean off. Cas is just getting started on dinner, letting Ozzy roam free around the apartment, when his roommate gets home, Cas can hear the dog’s nails tapping on the wood floor as he goes running to see who’s just entered the apartment.

“What on- son of a bitch. Cas!” Dean shouts from the entrance. “Cas, a dog got in?”

Castiel’s trying to fight back his laughter as Dean comes into the kitchen holding the dog in one arm. Ozzy has his tongue out, tail wiggling from side to side happily. Dean’s looking down at him, confused.

“Oh, no, I adopted it,” Cas deadpans. “And I can’t take him back because they’d charge me a very expensive fine. I’ve always wanted a dog, it helps with my anxiety.”

“Oh,” is all Dean responds. Cas smiles an evil smile as his friend looks down at the dog, studying it as if it were an alien…

But then Dean laughs and holds the dog in both arms, looking down at it with a fond expression in his face and Castiel’s smile falls. “It is so ugly, I love it,” Dean says. It is true, Ozzy’s a very weird looking, downright ugly dog. He’s round, almost cylindrical, has no neck whatsoever, has a very pointy, small snout and tiny skinny legs. The last thing Cas would have ever imagined was that Dean was going to find its ugliness _cute_.

“Wait, so you’re okay with it?” Cas asks in a high pitched voice.

Dean walks out of the room with Ozzy in his arms, laughing at the dog’s stupid face. “Sure, if it’ll help with your anxiety.”

It doesn’t. Ozzy cries at night a lot. Why, Castiel has no idea because he can’t get the dog to shut up, but it drives Cas insane because he can’t sleep properly the entire week the dog’s there with them. Dean, in the other hand, is a heavy sleeper, wouldn’t wake up if the house were on fire and his life depended on it. He apparently also doesn’t seem to notice how the dog’s nails tap on the wood every single step Ozzy takes, but Castiel, who enjoys utter silence when he’s reading boring things from school, does.

It only gets worse when Dean seems to quickly get attached to the dog. He usually has the round animal on his arms when they’re watching a movie, or asks Castiel to accompany him whenever he takes the dog out for a walk, because he does that now, even though Cas never asked him to. He feeds it, he spoils it, he scratches its belly... And Castiel feels guiltier by the hour because the dog’s going on a couple of days and the last thing he wants is to hurt Dean’s feelings by taking away something he loves. He doesn’t know how to tell him it was all a prank, that they can’t keep the goddamn dog and frankly Cas doesn’t _want_ a dog, it isn’t half as fun as he thought it would be.

Dean’s okay when the dog goes away back to his owner, though. Apparently, he did know Inias and his dog Ozzy after all... Not that he ever tells Castiel that.

3

The third time he tries to mess with Dean, they both end up inside a dumpster. To be fair with himself, at least this time Dean _is_ upset, just not the way Cas wanted him to. Also, he didn’t plan on ending up fishing for money inside trash either, he certainly doesn’t enjoy that at all.

This time, Castiel tries to directly screw with something Dean loves: his books. Dean takes pride on his books; they’d old versions, worn out by the use, kind of smelly honestly, and Dean says they’re classics, very good books Cas should read some day. He buys new versions of all of them, hardcover with also the new, mainstream cover that usually has some sort of illustration that Dean hates so much.

“The originals are just better,” he always says. He takes his books seriously.

He takes the old books, packs them in a box and takes them to Gabriel’s to hide them.

When Dean comes home, it takes him a couple of minutes to realise there’s something strange about the way the living room looks. He narrows his eyes, staring at the bookshelf, confused, then gasps, horrifies, and drops his backpack on the floor with a loud _thud_.

“What did you do!?” he yells at Castiel, way too intensely angry, way too loud. He’s never before snapped at Cas like that.

His friend just blinks a couple of times, making himself small, surprised by such a strong reaction. “I bought new versions of your books,” he tells Dean in a small voice. Years later Dean will laugh and say Cas looked like a small child being scolded for something real bad, but he isn’t laughing now.

Dean holds his head in his hands and start to hyperventilate. “Where the hell are my books, Cas?” he growls.

“I gave them away?” Cas half tells him, half asks, wondering if he should stop already with the prank and just confess they’re safe and sound at Gabriel’s.

“Please tell me you looked inside them first!” Dean’s eyes are wild and fearful. Castiel wishes he could say yes but he merely shakes his head no once. His best friend looks so angry at him, Cas could cry, they’ve never had an argument like this before. “Do you have any idea what you’ve done? I have like two thousand dollars hidden inside them, you big idiot!”

Years later Castiel will also tell him it’s stupid to hide money inside books, that’s what banks are for, even if Dean doesn’t trust them, but today’s not that day; today’s Castiel’s too afraid to say anything remotely sassy.

“Please, don’t be angry, Dean!” Cas begs in a hurry. “I didn’t _really_ throw them out, I was just messing with you. They’re at Gabe’s, in a box.”

Dean drags his friend out of the apartment and in a hurry they drive to Kali’s. Castiel’s itching to get to the damn box and show Dean everything’s okay, but the only problem is apparently she’s had a huge fight with Gabe and threw his things out. She won’t even open the door to them but she tells Cas where to find his brother...

“He’s out in the garbage, where he belongs!” she shouts at them from her balcony.

“What the hell did he do?” Dean mutters to Cas, who merely shrugs.

It takes them a while to find Gabriel; the apartment complex consists in several buildings and they have to round several of them to finally find the dumpsters. Gabe’s there, inside one of the three large metallic compartments, digging for his stuff. Dean and Cas break into laughter as soon as they see him; he’s got a banana peel he hasn’t noticed hanging from his shoulder.

“Quit laughing and come dig with me, she threw your box out too, smartass, and the garbage truck is coming in about an hour!” he snaps at them.

Dean mutters all sorts of curses while they dig in the garbage for his books. He swears if he cuts himself with something and gets some sort of disease, he’s going to sue Castiel. Cas, in the other hand, is on the verge of tears the entire time, doing quick math in his mind while he opens strangers' bags of trash, trying to figure out how he’s going to spare two thousand dollars from his pathetic salary to repay Dean if they don’t find the books. However, they do find them eventually, along with the rest of Gabriel’s stuff. When they return home, Dean sighs his anger and fears away, and unexpectedly hugs Cas. They smell awful, their clothes are probably going to stink for ages, and they both need a shower, but for a moment Dean just holds him while Castiel tears up and whispers apologies over and over again.

“It’s okay, Cas, no permanent harm done. I’m sorry I yelled at you, by the way,” Dean tells his friend in a soft tone, then he shoves him playfully, punches him in the shoulder and glares at him, “but if you ever mess with my books again, I’ll burn your tea, Cas, I swear to God I’ll burn all of it, even the fancy one from Japan!”

4

When he tries to prank Dean a fourth time, he actually does it right and it works, mostly, but he ends up more flustered than Dean at the end.

While Dean’s out with Charlie one night, he ventures into his roommate’s bedroom one more time to meddle with his belongings. This time he chooses something that he thinks is absolutely replaceable and has no sentimental value or important things hidden inside it; Dean’s underwear. That’s mistake number one because  when he pulls the drawer out until it’s almost about to fall from where it’s hanging from the dresser, at the bottom of it, hidden behind a mountain of socks, there’s a long, small box with an illustration on the side of a very realistic dildo. Cas gulps, pretends he doesn’t see it, then convinces himself he is _not_ wondering when Dean uses that or, most importantly, what he looks like when he does, then proceeds to steal all of Dean’s boxers and replaces them with lace panties for women. He puts the original underwear in a bag and hides it under his bed.

The following morning, he leaves before Dean’s even awake and he giggles like an idiot all the way to work, knowing Dean will take a shower when he wakes up and will have to go commando all day. Castiel knows his friend hates wearing no underwear and only ever does it in extremely rare occasions when he forgets to do laundry and Cas refuses to do it for him to teach him a lesson for laughing at him for trying to set a cleaning day for the apartment.

Later that same day, Castiel’s home before Dean. He’s sitting on the couch working on some boring assignment -“why did I choose accounting?” he mutters under his breath- when Dean storms into the apartment and stands in front of him with his hands on his hips, glaring down at his best friend.

“Cas! What the hell, man?” Dean fumes.

Castiel begins to chuckle, hiding most of his face behind some papers. He feels high with the joy. It’s like he’s finally part of something, he’s proved to be a typical idiot guy who pranks his friends and he loves it, relishes in Dean’s annoyance.

“Oh, you think you’re so funny, huh?” Dean narrows his eyes at him. “Cas, I had to sit straight all fucking day long in case my jeans got too low and my classmates got a peek of my _lacy panties._ ”

Castiel almost chokes on his spit.

“Wait a minute, you’re actually _wearing_ it?” he gulps, blushing hard. He scans Dean’s body as if he could see him wearing the women’s underwear by sheer will.

"Of course I am! Did you think I was gonna go commando?” Dean asks.

“Well, yes, actually.”

“No way, dude, jeans always get me chafed down there, I hate it. The lace is better, it’s soft, quite comfortable to tell you the truth, but not to go to _class_ , asshole."

“Oh,” is all Castiel can get out. He _feels_ the heat in his face, his ears and he just stared up at Dean, trying hard not to look down again.

He holds Dean’s stare looking like a deer caught in the headlights, probably for longer than he should, giving himself away, because next thing he knows Dean snorts and crosses his arms over his chest, lifting an eyebrow at him.

"What, you wanna see me wearing them, Cas? You kinky bastard," he teases his roommate with a smug grin.

“No! No, no, no,” Cas replies, shaking his head too many times, backing towards his room. “Forget about it. My apologies, Dean. I’ll give you your underwear right now, yes, right now…”

Castiel feels pretty confused when he jerks off to the image of Dean wearing the lace panties that night. He can’t help getting aroused when Dean says he’s going to bed early and then he hears small noises coming from his friend’s bedroom. He can’t help but think Dean’s using that toy he found earlier in his drawer. One thing leads to another, and he ends up masturbating for the first time ever to the thought of Dean, which also causes him to feel guilty in the morning.

When Gabriel asks how the prank went during lunch, Castiel blushes automatically. He feels dirty and stupidly fears Gabe will be able to read his mind and find out about everything that happened. It’s one thing to fancy Dean in private, in _secret_ , but it’s a whole different thing to admit it to someone else.

“N-nothing,” Cas stammers, looking anywhere but at his brother. “Nothing, he barely cared.”

Gabe sighs and rolls his eyes. “Cas, I thought you were supposed to be a smart guy. Didn’t it ever occur to you that you can’t prank Dean because he can’t get mad at you because the dude’s been in love with you since, hmm, let me think-- _forever!_?”

“We’re just friends,” Cas replies out of instinct. It’s not the first time Gabriel says things like this, but Castiel just can’t believe someone like Dean would be into someone like him.

“Oh, Cas, I wish, I so wish it were that simple between you two idiots…”

5

He’s not sure how the last attempt goes wrong; he’s seen Dean do this all the time, get drunk and stupid and annoy Cas non stop, so he hadn’t expected it to backfire on him when he did the same, but he can’t say he’s sorry for the result at all.

Cas hasn’t been drunk since the day he totally blacked out and tried to convince Dean and Balthazar to have a threesome with him, _after_ he made out with two different people at the bar. That was back in the day when their friendship was quite new. It was established since then that a drunk Castiel is a slutty Castiel, a very amusing thing to watch, a once in a lifetime gift to humanity, although it requires constant surveillance in case some pervert tries to take advantage of him. Dean’s always begged him to get that drunk again because he finds it hilarious apparently, but Cas felt like he made a fool of himself that day so he vowed never to drink too much again. He prefers to be the parent friend who watches the rest get drunk and makes sure they all get some safely. Dean does it all the time, trusts Cas to watch over him and get him home in one piece.

Tonight, he decides that he is going to push Dean’s button. His friend always does it, always teases and annoys the shit out of Cas when he’s drunk. He gets all flirtatious in a way he never allows himself to be when he’s sober, winking at him, trying to undo the first buttons of Castiel’s shirt, stealing his tie. He tries to drag him to nonexistent dance floors because he knows Cas hates to dance or begs him to sing a song with Dean on stage in that one bar that has a karaoke machine. Dean will always try to help Castiel hook up with a stranger, listing all the things his ‘devastatingly handsome friend’ has to offer, while said friend just tries to hide somewhere while blushing like a schoolgirl. He hugs him too tight, shoves him playfully way too many times, usually with more force than he realises, forgets that personal space even exists on the first place, and puts all his weight on Castiel when they walk home. All in all, Dean gets pretty physical, which he never is when sober. They do this over and over again in an endless loop every time they go out; Dean always parties hard and he always demands his best friend is right there by his side.

This time, though, it’s Dean’s turn to suffer an annoying drunk person messing with him all night, except Cas won’t be really drunk, just pretending to be. It’s a simple idea, he can’t go wrong with this. He’ll just annoy Dean for a couple of hours and also teach him a lesson; looking after drunk people isn’t always fun so if Dean could tone down his drinking, it would be great.

He knows it’ll work because whenever someone recalls the events of the night Cas blacked out, they all laugh at Dean too, who ran after him all over the club making sure no one made a move on his drunk friend while also trying to deflect Cas’ advances on him. Charlie says she never knew whether Dean was red from running or blushing, because he is a disaster bisexual who doesn’t know how to deal with guys hitting on him even though he’s been out of the closer _for years_.

Castiel puts Dean through everything he has to endure when his roommate is drunk. He sits way too close to Dean even though it’s hot in the bar. He leans closer and smiles at him, looking down at those lips Cas admits to think about from time to time, and Dean always gulps a little and looks away. Castiel innocently pats his knee, sometimes going a little higher for his thigh, which causes Dean to jump in his seat. He forces Dean to sway inelegantly with him in something that’s supposed to resemblance dancing. Dean allows it, mostly to keep other men away from Castiel and to tell them to fuck off when they try to hit on him.

“He’s drunk, man, come on, walk away, walk away,” he tells them in a disapproving tone.

Cas makes Dean walk in the cold winter night to that store that’s open 24/7 three streets away to buy a popsicle, then they get back to the bar. He sucks at it almost obscenely and Dean shoots angry looks at any dude who stares at his friend for too long. Dean’s not nearly as rattled or annoyed as Castiel wants him to be, so at some point he just starts introducing him to random dudes, listing all the things Cas likes about him.

“M’friend here- he’s a mechanic, the sexy kind,” Castiel beams, winking at Dean, who averts his eyes and blushes.

“Cas, quit it, man, I’m not looking for a hookup tonight,” Dean mumbles into his ear.

A guy actually offers Dean his number, which finally has the usually sassy Winchester speechless.

“Ah, Dean, you’ve made a friend!” Castiel teases him, pretending to sway in his feet. Dean puts a hand on his forearm to steady him. Cas leans closer, way too close, and Dean just freezes, holding his breath and all. “What do you say we finally have that threesome I offered you years ago, huh? I’ll bottom.”

“I’m in!” the guy standing in front of them says with an eager expression on his face, looking back and forth between them.

“Okay, alright, no, that’s enough, we’re going home!” Dean snaps and drags Castiel out of the bar before he can protest or take that stranger’s number.

Castiel laughs so much while walking home he _does_ feel a little drunk, drunk with the power of annoying Dean.

Dean takes Cas to his bedroom and tells him to get out of his clothes while he goes to the bathroom to get a bucket in case he pukes, and a glass of water. When he comes back, Castiel has his eyes closed and he actually is half drifting off to sleep already. Dean sits next to him, on the edge of the bed, and sighs. The movement of the mattress alerts Cas that Dean’s back and he rolls to his side, continuing to pretend.

“Wish you were like this when you’re sober, Cas. Except I don’t want to share you, you idiot,” Dean whispers softly, probably thinking Cas is already sleeping. Softly, tenderly, he combs Castiel's sweaty hair back with his fingers. “I want you all to myself.”

Castiel’s eyes fly open.

"Wait, what?" Cas sits right up, eyes wide and wild but focused and alert.

Dean startles and gulps, completely taken aback. "What the- I thought you were- Jesus, Cas, were you _faking_ sleep? Were you faking to be drunk too?"

"Yes, I was!” Castiel replies in a high pitched, completely panicked voice. “Were _you_?"

Dean opens his mouth to retort, then closes it again. He merely stares back at Castiel in a mirror of the same gay panic as his best friend is displaying.

“Oh, my _God_ , Gabriel was right, you’re into me!” Cas exclaims a moment, hitting himself on the forehead with the palm of his hand.

Dean tries to jump out of bed, away from Castiel, already beginning to rant that he’s wrong, that Gabe doesn’t know anything, or Charlie, or Benny, but Cas follows him and pulls him back to bed, pressing a bruising kiss against his lips. It doesn’t take long for Dean to snap out of his shock and return the kiss, forcing Cas into the mattress, licking inside his best friend’s mouth like he’s dreamed about a thousand times. When they stop kissing, it’s only because they need to breathe, but Dean lingers close to Castiel, leaning his forehead against the other’s while they breathe the same air.

“So you were pretending all night? Wish you would have told me earlier, before you made me buy a whole round of drinks for the entire bar,” Dean complains, playfully biting Castiel’s lower lip in retaliation.

“I’ll pay for that,” Cas chuckles. “But you’re not really mad, are you?”

Dean sighs. “No,” he admits. “I can never stay mad at you.”

“Because you love me?”

Dean closes his eyes, a little embarrassed, but nods and plants a sweet peck on Castiel’s lips. “Because I love you... so quit trying to prank me.”

**Author's Note:**

> Comments and kudos are much appreciated!


End file.
